A Cautious Man Ch. 01-05

This story was inspired by an old Bruce Springsteen song of the same name and used without permission. Sometimes, being careful doesn't always work out.

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A Cautious Man: Chapter 1

Bill Orton was a cautious man. He was also a skillful, organized, disciplined, and thoughtful man. Even at age five, his parents were impressed with his neatness and organization. His clothes, his toys, and his schoolwork were all placed in an orderly, specific manner in his room. He rose at the same time every day. He was never late for any meal, school, or church. He dressed neatly and never came home in a disheveled or unkempt state without good reason.

Young Bill was also curious. When a toy broke, he would examine it to see what had happened and attempt to repair it. Now and then he succeeded. As he got older, he became very analytical about how things worked. His curiosity led to discovery, which led to knowledge. With his father's encouragement, he learned all there was to know about the inner workings of the gasoline engine, electric motor, and a variety of mechanical devices that were found around the house. He got great satisfaction as he restored an old toaster or vacuum cleaner to operating status.

As Bill entered high school, he was an enigma to his schoolmates. It wasn't that he was shy or withdrawn, but no one in his class could say they knew him well. Bill just didn't let anyone get too close. He had a small number of male friends, and while a few of the girls wanted to get to know him, most of them failed. Only Sandra Thompson was able to make any impression on Bill, but at best, it was a very tenuous relationship based on their partnership in chemistry class. Physically, Bill was of medium height at 5' 9" but deceptively strong. No one would call him handsome, but neither was he homely. He was just plain Bill.

He had a long fuse. It took quite a bit to anger Bill, or even draw a heated response from him, but when he reached his breaking point he was a dangerous opponent. When he was sixteen, a bully from the senior class decided to provoke Bill with taunts about his quiet nature. Unable to elicit a response, the young punk decided to push Bill around, all the while spewing epithets concerning Bill's family and his heritage. He never saw the punch that decked him. It caught him flush on the chin and his lights went out immediately. By the time he had picked himself up off the ground, Bill had disappeared along with the bully's audience. After word got around, no one bothered Bill again.

Bill was an average-to-above-average student in school. It wasn't because he wasn't smart, but his interests lay in the mechanical world while his studies involved wider subject material. He did fairly well in mathematics because he spent a lot of time on his homework. He passed chemistry with Sandra's help and he did well in physics because he knew it was important to his main interests. He struggled in history, English and Spanish classes. It wasn't for a lack of effort, but it didn't come easily to him and it took all his energies just to pass the required courses. He had one very important thing going for him however, his teachers. Every one of them wanted him to succeed. They saw his effort and dedication and exemplary behavior, and they gave him every opportunity and assistance they could legitimately provide.

Bill was the only child of Fred and Violet Orton. They were a happy, middle-class family living on the outskirts of Cambelltown, in a three bedroom brick bungalow with a basement and a detached garage. Fred Orton was an accountant at the local furniture factory and Violet was a stay-at-home mother. They loved their son, Bill, and yet never spoiled him. Fred was also mechanically inclined and an all-around handyman. He encouraged Bill with his interests and was outwardly proud of his son and his accomplishments. He was a highly motivated young man and a diligent worker. He may not have been the quickest, but he was the most thorough and his work seldom, if ever, required correction.

The Ortons owned one car until Bill was 17, when he spent most of his savings to purchase a used, mid-sized pick-up truck with a camper shell. A local printer produced 500 single page flyers for Bill, advertising his services as a handyman. Within six months, Bill Orton had successfully combined his school work with his entry into the entrepreneurial world. He was now officially a businessman.

Bill's father volunteered to help him with his bookkeeping and tax responsibilities. When Bill graduated from high school, he had an established and profitable business. Bill thought there would come a time to think about expansion. He was working out of the family home and that couldn't go on indefinitely. He discussed his ambitions with his father and handed him his written business plan. His father looked at it and endorsed the concept. It was conservative and very well thought out. As he leaned back in his easy chair, reading his son's prospectus, he was smiling to himself. His son was everything a parent could hope for. If only he could find a way to help him with his personal relationships. Bill was a loner and Fred worried that it would hinder his future happiness. He wasn't sure if Bill had ever even had a date.

Fred and Violet met at a local church social. Fred was studying accounting at night school and working in an office during the day. Violet Shepherd was a cashier at the supermarket and had just broken up with her long-time boyfriend who had decided he was going to join the Navy. She had no ambition to live in married quarters on some naval station, waiting who knows how long for her husband to return from sea duty. She wanted a steady, reliable man who would be home for supper every night and would love, protect, and provide for her. She had no unrealistic ambitions.

Neither Fred nor Violet would be described as beautiful people. But beauty is, after all, in the eye of the beholder. When they met at the social, they were almost immediately attracted to each other. They sat and talked, and at the end Fred asked Violet for a date. She immediately said yes. They dated for three months before they became intimate. Both of them virgins, it was an awkward union to begin with, but over time they became comfortable with each other and even a bit adventuresome. Eventually, Fred produced a ring and they set a date.

They had been married two years when Violet happily announced to Fred that she was pregnant. She quit her job at the supermarket and stayed home awaiting the birth of their first child. All went well until the third trimester when Violet began to have some problems with fatigue and her breathing and was diagnosed with an irregular heartbeat. Bed rest was ordered and when she finally delivered, it was a healthy son, William Frederick Orton, 7lbs. 9oz. Her doctor advised her against becoming pregnant again. As was the custom at that time, she was referred to a gynecologist, and a hysterectomy was performed. The Ortons' were resigned to being a one child family.

Chapter 2:

Bill lost his virginity a few weeks before his twenty-first birthday. It didn't happen in a usual or predictable way. It wasn't expected or planned, it just happened. He had been called to the home of Darla and Gordy Therrien. Apparently, there was a problem with the kitchen sink and the garbage disposal unit. Bill had plenty of experience with this type of problem. People were invariably putting silly things down the sink with the mistaken idea that the noisy, thrashing sound would look after it. He was sure this was another jammed machine with bent blades and possibly a burned out motor. If it was both, it wouldn't be worth fixing. He had a couple of spare, sealed motors that might do if they would fit the casing. He would just have to pull it apart and see what was needed.

Darla Therrien was about to step into the shower when she heard the doorbell ring. She cursed, thinking that the repair man wouldn't be calling this early, would he? She pulled her robe on over her naked body and walked to the front door, looking through the peep hole first. She didn't recognize the young man, but she could see his truck in the background and she was sure it was young Orton. She opened the door to him.

"Good morning, ma'am. I'm Bill Orton. I'm here to see about your kitchen sink." Darla was impressed. He was dressed neatly and he was polite. Surprisingly, he was also quite young.

"Come in. I'll show you the problem," she said as she led him to the kitchen. She stepped to the sink and turned the water on. It wasn't draining very much, if at all. She pressed the switch on the disposal unit and all that could be heard was a humming sound. Bill reached around her and turned the machine off.

"It's jammed, ma'am. I'll need to take it off and clean it out. Sounds like the motor is OK, so I should be able to repair it." He was smiling at the woman as he reassured her.

Darla smiled back at him. "So polite and quite handsome looking too," she thought. It had been a while since Gordy had run off with that skinny floozy, Carlotta. She had been lonely and often horny. She appraised the young repairman as she stood only a few feet away, watching him as he ducked under the sink to begin his work.

"This is going to take a bit of time, ma'am. If it's OK, I'll work here on the kitchen table. I have a protective cover so that it doesn't get marked or dirty."

"You go ahead ... uh ... Bill is it?"

"Yes, ma'am."

"I'm Darla ... you don't have to call me ma'am. It makes me feel old," she said, somewhat surprised at her own comment.

"Yes, ma'am ... I mean, Darla." He didn't sound very sure of himself.

"I'm just going to take my shower. I'll only be a few minutes."

Darla Therrien walked down the hallway of the bungalow and turned into the single bathroom, glancing back toward the kitchen before closing the door behind her. She was strangely aroused for 8:30 in the morning. She had been going without the company of a man, her man, for six months, and it was harder than she thought it would be. She took off her robe and looked at herself in the mirror.

She was thirty seven years old and her figure could most politely be described as "roly-poly." She was round in every location. Her face was round. Her large breasts were round, although beginning to sag from their own weight. Her belly was round and her butt was two, flawless round mounds. Her thick thighs were smooth and unwrinkled, but they were short, ending in thick knees and strong calves. She was just a little over five feet tall and she felt like she was a human bowling ball.

Until Gordy had run off, none of it had mattered. He loved her, and my god was he good in bed. He would light her up like a roman candle when they made love. Her orgasms were fabulous and plentiful. He would bury his face in her breasts and feast on her nipples. And god, could he eat her out. She got wet just thinking about it. But all that was gone now. Their last time together was the night before he left and it was as wonderful as it always was. She had no inkling of what was to happen. The note on the kitchen table the next morning told the whole story in five sentences. She was devastated.

She finished her shower and was about to go to her bedroom to change into her usual jeans and t-shirt when she stopped and looked again at herself in the mirror. She put on her robe and walked to the master bedroom and selected her one and only muumuu. It was a souvenir of their vacation in Hawaii a few years ago. Gordy and earned a big bonus and they decided to take "The Vacation of a Lifetime." It was. They spent ten days in the Islands, and nine nights making love. It was wonderful and Darla thought of those ten days often. She removed her robe and, without putting on any underwear, slipped the bright, aquamarine colored garment over her head. She deliberately left the top two large buttons undone.

She returned to the kitchen to find Bill sitting at the kitchen table with the garbage disposal unit on the table in front of him. It was in a state of disassembly and there must have been twenty different parts all arranged in some specific order on the table. She leaned over to inspect the inner workings of the unit, thereby giving Bill a close-up view of her breasts if he looked up. He looked up. He first glanced at her face to see what she was looking at and then, as his eyes dropped, he saw the swaying breasts of Darla Therrien less than two feet from his face.

"How's it going?" Darla asked innocently. She knew exactly what he could see and the sway of her breasts was deliberately invoked by the movement of her shoulders. The seduction of Bill Orton had begun.

"Uhhhh ... fine. Just some fibrous stuff ... jammed in the blades. I can fix it OK." he stammered. He had turned crimson as he desperately sought a way not to look at her breasts. He looked down at the table, but his hands were no longer moving. He was locked in place, uncertain what to think or say or do.

"Your taps are leaking," he finally managed. "I'll put in some new washers while I'm here. It'll save me having to come back."

"I wouldn't mind if you came back, Bill." She said it with a hint of innuendo that was lost on the young repairman.

"It'll save you some money, ma'am ... I mean Darla. It'll only take me five minutes." Bill went back to his work and within a few minutes had reassembled the disposal unit, re-installed it under the sink and replaced the tap washers. A quick test confirmed everything was working properly.

"Do you have a girlfriend, Bill?" The question had come out of the blue and Bill was totally unprepared for it.

"Ah ... no ... no ... I don't. I guess I've been too busy with my business to find the time." He was clearly uncomfortable.

"Well, I don't have a husband any more. I suppose you heard ... he took off with that Carlotta Thurston. I guess he thought she was prettier than me." She couldn't hide the disgust in her voice, and it was directed at Carlotta.

"I heard about that." In a small place like Cambelltown, word travels fast. "I'm real sorry. He shouldn't have done that to you." Bill was surprised at how strongly he felt about her loss. He thought Gordy Therrien had made a big mistake. Darla was a nice lady and didn't deserve what happened to her.

Darla was also surprised. He had sounded very sincere with his comment and she smiled her thanks to him, all the while leaning over the table once again to give Bill another view of her ample cleavage.

Bill was almost hypnotized by the swaying breasts of the buxom woman. He couldn't seem to tear his eyes away from them. It was noticed immediately by Darla.

"Have you ever seen a naked woman, Bill?" It was such an outrageous question that Bill was stunned into silence.

"I guess not. You've lived a sheltered life. I can tell from just how polite you are and just how fascinated you are with my boobs. Would you like to see my boobs, Bill? Would you like to touch them? Maybe, kiss them? I bet you would." She was almost taunting him now. She began to pull the Muumuu up over her head, revealing her naked body to Bill. He was shocked into immobility in the kitchen chair, unable to move, watching every part of her body as it was revealed. He truly had never seen a live, nude female before and he was fascinated. She was very round and very feminine, but not in the movie star fashion. Her skin was flawless and unwrinkled and seemed to be stretched tightly over her rotund figure. The hair covering her sex was a different colour and texture from the hair on her head.

Darla moved toward Bill and as she came to his side, she held and then pressed her left breast against his lips. Bill's eyes were fixed on her face, but almost involuntarily, he began to suckle at her breast. He could feel the nipple extend and become hard and he used his tongue to lick it, at first gently and then with a bit more intensity. Darla held her breast to his face and began to feel the stirring in her groin as the sensations Bill was creating travelled through her. She smiled at him and he continued to watch her. Finally, she withdrew her breast and exchanged it with the other. Bill needed no encouragement to continue.

Darla lifted her leg and straddled Bill in his chair, finally lowering herself onto his lap. Her hands clasped his face and she tilted it up from her breasts to her lips and she began to kiss him deeply and passionately. At first, Bill didn't respond, but it wasn't long before he probed her mouth with his tongue, and his hands began to massage her breasts. He was going on instinct and hoping that he was doing it properly.

After an extended period of kissing and fondling, Darla stood and took Bill's hands. Wordlessly, she pulled him up and then turned and led him down the hallway to her bedroom. Bill followed as if he were a child being led to his room. Darla pushed him down on the edge of her bed. She looked fondly at him before she kissed him lightly on the lips.

"You're a virgin, aren't you Bill?"

He nodded, his eyes wide and fixed on Darla's face.

"That's nice. I'm going to teach you everything you need to know about pleasing a lady. When you and I are done, I bet you will be a wonderful lover and some young woman is going to be very happy having captured you." She said it so gently and softly that it sounded like a mother talking to her son, soothing his fears. It was exactly the right thing to do. Bill began to relax a little, but was still very nervous about what was to happen next.

Darla began to help Bill remove his clothes. First, his shoes, then shirt, pants, socks and finally, his underwear. Bill was very uncomfortable being naked in the presence of this very insistent woman. He was completely unable to anticipate what might come next. He had decided to leave it all up to Darla and let her guide him. He was excited. He was to become a man this morning and no longer would he feel that he had been left behind. He would be "one of the boys" at last.

"Bill, I know this is all new to you and I know you are nervous. I want you to relax and let me show you how you can give and receive pleasure with a woman. I do hope you want me to do this for you. I really do want to, you know."

They were reassuring words. Bill nodded and offered a weak "Yes, ma'am ... Darla," as she held his shoulders and looked directly into his eyes. She smiled a broad smile and kissed him lightly on the lips.

She began with working her way down his compact body and landing butterfly kisses on his nipples, licking the nipples and causing Bill to react to her actions. She continued on down until she reached his groin and she immediately felt tension in Bill's body. He was unprepared for what Darla had in mind next. She softly grasped his slowly growing erection and began to stroke it. Within seconds, it was even harder and standing straight out as she held it. She looked up at his face and could see the intensity that he felt as he watched her and waited for what was to come next.

Darla smiled at him and then bent her head to lick the pre-cum from the glans of his rigid cock. Bill reacted violently as he felt her warm tongue on his private part. His hips snapped upward and he gasped as he experienced this strange, new feeling.

"Relax, Bill. You're going to love this, trust me." Her reassuring words helped as he tried to exhale and let his contracted muscles return to normal. It was like waiting for a needle at the doctor's office; only this was the anticipation of pleasure, not pain. He closed his eyes and willed himself to wait and let Darla look after the rest.

She smiled to herself as she saw Bill battle his emotions, trying to comprehend these new sensations. Darla returned to her task, and began to lick the length of his cock. It wasn't any longer than normal, but it was definitely much thicker than any she had experienced, including Gordy's prodigious member. But what Gordy had in length, Bill had in girth. She couldn't wait to feel herself stretched around his lovely, young penis. But first, some lessons in foreplay.